US3512913A - Dyeing polyethylene terephthalate film - Google Patents

Dyeing polyethylene terephthalate film Download PDF

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Publication number
US3512913A
US3512913A US565935A US3512913DA US3512913A US 3512913 A US3512913 A US 3512913A US 565935 A US565935 A US 565935A US 3512913D A US3512913D A US 3512913DA US 3512913 A US3512913 A US 3512913A
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film
dye
bath
polyethylene terephthalate
dyeing
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Michael Curtis Day
Patrick Terence Mcgrail
Basil R Shephard
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Bexford Ltd
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Bexford Ltd
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B3/00—Passing of textile materials through liquids, gases or vapours to effect treatment, e.g. washing, dyeing, bleaching, sizing, impregnating
    • D06B3/10—Passing of textile materials through liquids, gases or vapours to effect treatment, e.g. washing, dyeing, bleaching, sizing, impregnating of fabrics
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06B—TREATING TEXTILE MATERIALS USING LIQUIDS, GASES OR VAPOURS
    • D06B2700/00—Treating of textile materials, e.g. bleaching, dyeing, mercerising, impregnating, washing; Fulling of fabrics
    • D06B2700/09—Apparatus for passing open width fabrics through bleaching, washing or dyeing liquid

Definitions

  • This invention relates to the dyeing of polyethylene terephthalate film by a continuous process.
  • polyethylene terephthalate hereafter referred to as polyester
  • polyester is difiicult to dye owing to its closely knit and partly crystalline structure, its resistance to swelling in aqueous liquids and in many simple solvents, and its lack of chemical groupings having a strong afiinity for dyestuffs.
  • Dyes of this kind are insoluble in water but produce suspension of dye of very small particle size. They are available commercially as powders or as granules, usually already containing dispersing or stabilising agents in addition to dye.
  • polyester film refers to amorphous polyethylene terephthalate film and polyethylene terephthalate film which has been monoaxially stretched, or biaxially stretched and heat set to produce a dimensionally stable and stronger base.
  • One method of orientating polyethylene terephthalate film comprises stretching the film at 80-100 C. in a longitudinal direction with a draw ratio of 2.5- .0 while the film is restrained from shrinkage in the other linear dimension followed by stretching the film at 80-120 C. in the transverse direction with a similar draw ratio while maintaining sufficient tension in the already drawn longitudinal direction to again avoid shrinkage.
  • the film is finally heated at 150-250 C. for some 0.5-5 minutes while being restrained from shrinkage in both dimensions; the object of such heat-setting and similar annealing processes results in a film showing little or no shrinkage on re heating to moderate temperatures on a later occasion.
  • film may also be drawn transversely "ice,
  • polyester film as used in the specification is a film of polyethylene terephthalate which has on its surface a coating of up toone micron in thickness, this coating being permeable to the dyes used in this invention.
  • Such coatings are usually coated on to the amorphous polyethylene terephthalate film before the film is biaxially oriented or during a stage of the biaxial orientation. The purpose of such coatings on the film is to prepare the film for further coatings resulting finally in commercial products.
  • polyvinylidene chloride copolymers which contain not less than 30 mole percent of units derived from vinylidene chloride with one or more types of unit derived from ethylenically unsaturated copolymerisable monomers including vinyl-chloride, acrylom'trile, methacrylonitrile, itaconic acid, acrylic acid, methacrylic acid, acrylic esters or methacrylic esters.
  • Polyvinylidene chloride homopolymers may also be coated in such a way and also any of the resins which constitute layer A of our co-pending British patent application 50,1 18/ 64.
  • polyvinyl halo-acetate or cyanoacetate polymers containing not less than 30 mole percent haloor cyanoacetate together 'with one or more types of unit derived from vinyl alcohol, vinyl acetate, acrylamide, methacrylamide, crotonic acid, N-methylol acrylamide or Z-hydroxyethyl acrylate.
  • polyethylene terephthalate film or polyester film as referred to in this specification relates to amorphous or monoaxially or biaxially oriented polyethylene terephthalate film and also to amorphous or monoaxially or biaxially oriented polyethylene terephthalate fihn which has on its surface a coating of up to one micron in thickness, this coating being permeable to the dyes used.
  • the continuous dyeing of polyester film may be efiFected at speeds of, for example, 10-100 ft./min. giving evenly dyed products.
  • Film dyed by the process of the present invention for example in light shades having optical density to white light up to 0.5, is ideally suited as a plastics base for the subsequent preparation of photographic film -for X-radiography, as a base for the preparation of drafing films and diazotype films, for the preparation of packaging films or for any other purpose where clear coloured polyester films may be used.
  • the surface characteristics of polyester film may be conveniently altered, if desired, so that the dyed film gives a stronger adhesive bond than undyed film to a layer of a polymeric material subsequently applied.
  • dyecarriers to dye-baths used for the dyeing of polyester fibres or fabric and that these substances accelerate dyeing and enable dye-bath temperatures of, for example, 100 C. to be used with dyeing times of about 1-3 hours.
  • the dye-bath For the continuous dyeing of polyester film at economic speed the dye-bath must be maintained at 80-100 C. for many days. However, it has been found that the presence of dye-carrier has a destabilising effect on the dye-bath giving, within 1-24 hours of heating, deposition of tarry material on the walls of the equipment and on the surface of the polyester film. Instability of the dye-bath, even in the absence of carriers, occurs during long periods of heating at 80-100 C. but addition of surface active agents or stabilising agents, in addition to those already present in the dye-stuff introduced during the preparation of the dye in a dispersable condition, improves the dye-bath stability. Many surface active agents may be used and an amount of 10-100% by Weight of the disperse dye used has been found most effective in baths not containing a dye-carrier while in baths containing a dye-carrier no sufficiently stable system was found.
  • a process for the continuous dyeing of polyethylene terephthalate film which comprises applying to a travelling web of the film a pre-treatment liquid containing dye-carrier and thereafter applying to the travelling web of the film a hot aqueous dye-bath containing a dispersed dye of a type suitable for the dyeing of polyethylene terephthalate.
  • the speed of dyeing of polyester film in a dye-bath, with or without dye-carrier present is much accelerated by temperature so that for instance, baths containing dye-carrier are normally maintained at or near the boil, that application of dye-carrier in a pre-treatment bath may be made at any convenient temperature and the temperature of this first bath has little influence on the speed of dyeing in the subsequent hot dye-bath.
  • the pre-treatment bath containing dye-carrier may be at any temperature between freezing or boiling point but preferably is used at 15-80 C., e.g. 2040 C.
  • a further advantage of the use of a pre-treatment bath maintained at, for example 20-40 C., is that there is little volatilisation of the dye-carrier (avoiding consequent loss and toxic hazard) compared with the conventional procedure of addition of the dye-carrier to the hot dye-bath.
  • a large number of dye-carriers have been proposed for the dyeing of polyester with disperse dyes.
  • Well-known carriers are phenol, orthoand para-phenylphenol, diphenyl, chlorinated benzenes and diphenyls, methyl salicylate, benzoic acid and benzyl alcohol.
  • a number of dye-carriers described by trade names are also available for use as additions to the dye-bath from suppliers of disperse dyes.
  • dye-carriers may be applied as a pre-treatment to films of polyester in many ways including use of aqueous solutions, aqueous suspensions, aqueous mixtures containing the dye-carrier in a solubilised form, aqueous solutions of alkali metal, ammonium or amine carboxylates or phenates where appropriate or as solutions or suspensions in organic solvents.
  • Some simple solvents such as the chlorinated hydrocarbon, for example methylene chloride, tetrachloroethane, chloroform or trichloroethylene, have noticeable swelling action on polyester and may also be used as dye-carriers.
  • aqueous solutions either saturated or less than saturated, of orthoor para-chlorophenol give simple, cheap and stable pretreatment baths which are very effective in that a brief immersion of the film web, for example for 15 seconds, is sufiicient to promote excellent dyeing in the subsequent hot-dye bath.
  • Polyester film dyed by the process of this invention may be further improved by cleaning and finishing treatments designed to achieve:
  • Treatments under (i) above may be to merely wash the film with water, preferably as soon as it emerges from the dye-bath, and dry the film.
  • the film may be washed with solvents, preferably acetone or methanol, or washed with solvents after washing with water. Washing liquids may contain surface active agents, and mechanical aids such as rotating rollers, brushes or wipers, simple wipers or air-knives may be used if needed.
  • Treatments under (ii) are best applied after washing. Improved penetration is not always required since the dyed film resulting from the present process and treated as under (i) is free from surface dye. However, if the dyed film is treated with organic solvents for any further purpose, especially if the solvents have a penetrating action on polyester, dye is liable to be lifted to the surface or entirely removed from the film. Three methods have been found to give improved penetration of the dye and these may be combined in various ways for maximum effect:
  • solvents having a slight swelling action on the film before treatment with dye-carrier, or immersing the dyed film from the dyebath in the vapour of solvents having a swelling action.
  • Suitable solvents are chlorinated hydrocarbons such as methylene chloride, trichlorethylene, chloroform or tetrachlorethane.
  • Treatments under (iii) are optional to improve adhesion in cases where coatings of polymeric materials are to be applied in further processes to the dyed film.
  • Organic solvent solutions of swelling agents for polyester such as the monodiand tri-chlorophenols are supplied by passage of the dyed film through a solvent bath containing one or more swelling agents by head coating or by any other well-known methods.
  • the film may be dyed with a mixture of dyes in one dye-bath although it is well known that as dyes are liable to have disparate propensity to transfer to the film the resultant colour tint of a continuously travelling web may gradually change. However, use of more than one dye, perhaps of similar colour, frequently faster dyeing or dyeing to a great depth of shade.
  • the film has applied to it a pre-treatment liquid containing dye-carrier and then a hot dye-bath containing one of the dispersed dyes followed by an aqueous washing and then the film has applied to it more pre-treatment liquid containing dye carrier and then has applied to it a second hot dye-bath containing the second dispersed dye.
  • the direction of the polyester Web 1 is indicated by arrows at the beginning and at the end of the web 1.
  • the web 1 passes over a series of driven rollers 2 and follows a pre-determined path through the various treatment baths A, B, C and D.
  • Treatment bath A is the dye assistant bath.
  • Treatment bath B is the dye bath.
  • Treatment bath C is the aqueous washing bath.
  • Treatment bath D is the acetone washing bath and E is the drying cabinet, wherein the web is dried by hot air.
  • E is the drying cabinet, wherein the web is dried by hot air.
  • Situated in the baths C and D are rotating scrubbers 4 which serve to remove any residues of dyestuif which may still remain on the surface of the web.
  • EXAMPLE 1 A polyester film was passed continuously through a bath A containing a 2.8% aqueous solution of parachlorophenol held at 40 C. at a speed providing an immersion time of 12 seconds. As the film left the bath, excess solution was removed by air-knives and the surface-dried film was passed into the dye-bath B held at 85 C. and was given an immersion time of 30 seconds.
  • the dye bath comprised an aqueous mixture of color Index Disperse Blue 26 63305 (0.2% w./v.) and dispersing agent (0.1% w./v.) Dye liquor on the surface of the film as it emerged from the dye bath was removed by airknives as on Bath A.
  • the blue film having an optical density to white light of 0.12 was perfectly evenly dyed and free from blemishes and was ideally suited for use as a base foil in the preparation of photographic film for X-radiography.
  • EXAMPLE 7 A freshly prepared latex of polyvinylidene chloride containing 10% solids was coated onto both sides of amorphous polyethylene terephthalate film. The coated film was heated at C. and drawn in the longitudinal direction with a draw ratio of 1:3.5 while the edges were re-strained from shrinkage, followed by transverse drawing at C. with a draw ratio of 1:3.5 while re-strain ing shrinkage in the longitudinal direction. The film was then heat-set for 3 minutes at 180 C. while further dimensional change was re-strained.
  • the coated, biaxially orientated film was dyed as in Example 1.
  • the presence of the very thin coating had no effect on the speed of dyeing or on the final density of colour obtained.
  • EXAMPLE 8 Amorphous polyethylene terephthalate film was first stretched longitudinally as described in Example 7 and this uniaxially stretched film was then coated with a latex of polyvinyl chloracetate containing 3% solids. Processes of further stretching, heat-setting and dyeing were continued as in Examples 7 and 1. The very thin layer of polyvinyl chloracetate on the biaxially orientated polyethylene terephthalate film did not affect the dyeing which took place as for uncoated film.
  • EXAMPLE 9 Amorphous polyethylene terephthalate film was coated with a terpolymer latex derived from the monomersvinylidene chloride, methyl acrylate and itaconic acid prepared as described in Example 1 of British Pat. 718,- 422. The coated film was biaxially stretched simultaneously in both linear dimensions at 100 C. with stretch ratios of 1:3.5 fol-lowed by heat-setting at C. for Zminutes.
  • the resultant film was dyed as in Example 1.
  • An aqueous dispersion of the product was prepared containing 5% solids and 5% methyl salicylate.
  • the aqueous dispersion was used to coat both sides of amorphous polyethylene terephthalate film when processes of orientation, heat-setting and dyeing were carried out as in Examples 7 and 1.
  • Polyethylene terephthalate film biaxially stretched and heat-set was passed continuously through a bath A containing a 2.5% aqueous solution of parachlorophenol at 25 C. at a speed providing an immersion time of 20 seconds. As the film left the bath, the excess solution was removed by air-knives and the surface-dried film was passed into a dye bath B held at 90 C. and was given an immersion time of 20 seconds.
  • the dye-bath comprised an aqueous dispersion of CI Disperse Blue 59 (0.4% w./v.).
  • the blue film from the bath was passed into a second bath of type A and then into a second dye-bath of type B but containing CI Disperse Orange 1, 11080 (0.4% w./v.) held at a temperature of 90 C.
  • the emergent orange-grey film was surface-dried by a pair of air-knives, passed into a bath of water to wash the film surface, redried by air-knives and finally heated for 3 minutes at 120 C. to accelerate diffusion to the dyes into the surface of the film.
  • EXAMPLE 13 Polyethylene terephthalate film was dyed as in Example 12 but treatment in a second dye-carrier bath A was omitted. Rather less of the orange dye was transferred to the film in the second dye bath B than occurred in Example 12 and the resultant product was grey in tint.
  • EXAMPLE 14 Polyethylene terephthalate film was dyed as in Example 12 using one dye-carrier bath A and one dye-bath B containing 0.4% w./v. of each of CI Disperse Blue 59 and CI Disperse Orange I, 11080. The film was dyed an even plain grey tint.
  • EXAMPLE 15 Polyethylene terephthalate film biaxially stretched and heat-set was dyed as in Example 1, 'but using a dye-bath containing 4% w./v. CI Disperse Red 92 and 93. The film was dyed pink.
  • EXAMPLE 16 Polyethylene terephthalate was dyed as in Example 1 using a dye-bath containing 0.4% w./v. CI Disperse Orange, 11080. The film was dyed a salmon-pink colour.
  • EXAMPLE l7 Polyethylene terephthalate was dyed as in Example 1 using a dye-bath containing 0.4% w./v. CI Disperse Yellow 3, 11855. The film was dyed a pale yellow colour.
  • Polyethylene terephthalate was dyed as in Example 1 using a dye-bath containing 0.4% w./v. CI Disperse Violet 25. The film was dyed light purple.
  • a process for the continous dyeing of unplasticised polyethylene terephthalate film which comprises in sequence the steps of feeding a travelling web of said film through an aqueous bath containing dye carrier, the web being immersed in the said bath as it travels through it, substantially removing any bath liquor from the surface of the web, feeding the web through a hot aqueous bath containing a dispersed dye for the polyethylene terephthalate, the web being immersed in said dye bath as it travels through it, removing dye bath liquor from the surface of the web and drying the web.
  • the dyecarrier is selected from the class consisting of phenol, ortho-para phenyl phenol, diphenyl, chlorinated benzenes, chlorinated diphenyls, methylsalicylates, benzoic acid and benzyl alcohol.
  • liquid containing dye-carrier is an aqueous solution of parachlorophenol.
  • a process according to claim 1 wherein the film subjected to said steps is a biaxially orientated and heatset film, and the bath containing the dye-carrier is an aqueous solution of para-chlorophenol having a temperature of 1580 C.

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  • Chemical & Material Sciences (AREA)
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US565935A 1965-07-26 1966-07-18 Dyeing polyethylene terephthalate film Expired - Lifetime US3512913A (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3637340A (en) * 1968-02-02 1972-01-25 Ciba Geigy Ag Process for the dyeing and printing of textile material made of hydrophobic polyesters
US3650663A (en) * 1969-09-15 1972-03-21 Collins & Aikman Corp Method for treating synthetic linear polyesters fibers and film in the vapor phase to improve the dyeability and to heat set said polyesters
US3753646A (en) * 1969-07-30 1973-08-21 Soltex Soc Civ New process of textile fabrics dyeing
US3893806A (en) * 1973-01-19 1975-07-08 Burlington Industries Inc Method for continuous warp dyeing polyester and blends of polyester on conventional pad-steam dye slasher
US3973902A (en) * 1972-10-07 1976-08-10 Hoechst Aktiengesellschaft Process and device for the continuous fixation of prints and pad-dyeings on polyester fibers and their mixtures with cellulose fibers
US4051295A (en) * 1974-12-20 1977-09-27 Bernstein Donald J Alteration-sensitive surface
US4142852A (en) * 1974-07-24 1979-03-06 Bruchner Apparatebau Gmbh Method for dyeing and finishing textile material
US4181498A (en) * 1975-09-23 1980-01-01 Sandoz Ltd. Dyeing and printing with synthetic thickeners
US5613986A (en) * 1993-05-17 1997-03-25 Hoechst Celanese Corporation Synthetic fiber dyeing process
US6221112B1 (en) 1992-07-15 2001-04-24 Cp Films, Inc. Process for producing a colored polyester film
US9630384B2 (en) 2014-03-07 2017-04-25 3M Innovative Properties Company Durable extruded dyed polyester films

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2188160A (en) * 1936-10-09 1940-01-23 Colancse Corp Of America Coloration of artificial textile and other materials
US3034847A (en) * 1957-10-01 1962-05-15 Du Pont Dyeing polyethylene terephthalate films with hot disperse dye-organic solvent mixture

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2188160A (en) * 1936-10-09 1940-01-23 Colancse Corp Of America Coloration of artificial textile and other materials
US3034847A (en) * 1957-10-01 1962-05-15 Du Pont Dyeing polyethylene terephthalate films with hot disperse dye-organic solvent mixture

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3637340A (en) * 1968-02-02 1972-01-25 Ciba Geigy Ag Process for the dyeing and printing of textile material made of hydrophobic polyesters
US3753646A (en) * 1969-07-30 1973-08-21 Soltex Soc Civ New process of textile fabrics dyeing
US3650663A (en) * 1969-09-15 1972-03-21 Collins & Aikman Corp Method for treating synthetic linear polyesters fibers and film in the vapor phase to improve the dyeability and to heat set said polyesters
US3973902A (en) * 1972-10-07 1976-08-10 Hoechst Aktiengesellschaft Process and device for the continuous fixation of prints and pad-dyeings on polyester fibers and their mixtures with cellulose fibers
US3893806A (en) * 1973-01-19 1975-07-08 Burlington Industries Inc Method for continuous warp dyeing polyester and blends of polyester on conventional pad-steam dye slasher
US4142852A (en) * 1974-07-24 1979-03-06 Bruchner Apparatebau Gmbh Method for dyeing and finishing textile material
US4051295A (en) * 1974-12-20 1977-09-27 Bernstein Donald J Alteration-sensitive surface
US4181498A (en) * 1975-09-23 1980-01-01 Sandoz Ltd. Dyeing and printing with synthetic thickeners
US6221112B1 (en) 1992-07-15 2001-04-24 Cp Films, Inc. Process for producing a colored polyester film
US5613986A (en) * 1993-05-17 1997-03-25 Hoechst Celanese Corporation Synthetic fiber dyeing process
US9630384B2 (en) 2014-03-07 2017-04-25 3M Innovative Properties Company Durable extruded dyed polyester films

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Publication number Publication date
GB1096229A (en) 1967-12-20
FR1487797A (fr) 1967-07-07
BE684622A (en)) 1967-01-03
NL6610465A (en)) 1967-01-27
LU51644A1 (en)) 1966-09-26
CH470530A (de) 1969-03-31

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